EP0710705A1 - Pigments jaunes de diketopyrrolopyrrole - Google Patents
Pigments jaunes de diketopyrrolopyrrole Download PDFInfo
- Publication number
- EP0710705A1 EP0710705A1 EP95810665A EP95810665A EP0710705A1 EP 0710705 A1 EP0710705 A1 EP 0710705A1 EP 95810665 A EP95810665 A EP 95810665A EP 95810665 A EP95810665 A EP 95810665A EP 0710705 A1 EP0710705 A1 EP 0710705A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- diketopyrrolo
- hydrogen
- alkyl
- formula
- pyrroles
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title description 11
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 239000011368 organic material Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000003233 pyrroles Chemical class 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- NKHUXLDXYURVLX-UHFFFAOYSA-N 2h-pyrrolo[3,4-c]pyrrole-4,6-dione Chemical compound N1C=C2C(=O)NC(=O)C2=C1 NKHUXLDXYURVLX-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- XNWKYUZPKRLNLJ-UHFFFAOYSA-N 1,4-di(phenanthren-9-yl)pyrrolo[3,4-c]pyrrole-3,6-dione Chemical class C1=CC=C2C(C=3C4=C(C(N=3)=O)C(C=3C5=CC=CC=C5C5=CC=CC=C5C=3)=NC4=O)=CC3=CC=CC=C3C2=C1 XNWKYUZPKRLNLJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- -1 phenanthren-9-yl Chemical group 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 229920003270 Cymel® Polymers 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- QKWILNTYPDJSME-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole-3,6-dione Chemical class C1=NC(=O)C2=C1C(=O)N=C2 QKWILNTYPDJSME-UHFFFAOYSA-N 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- CWFIYYOQYVYBPW-UHFFFAOYSA-N phenanthrene-9-carbonitrile Chemical compound C1=CC=C2C(C#N)=CC3=CC=CC=C3C2=C1 CWFIYYOQYVYBPW-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
Definitions
- the present invention relates to new yellow diketopyrrolopyrroles and their use as pigments.
- 1,4-Diketopyrrolo [3,4-c] pyrroles have been known for some years as red pigments with excellent pigment properties, for example from US Pat. No. 4,415,685, where diketopyrrolopyrroles of the formula wherein R1 and R2 are isocyclic or heterocyclic radicals, preferably mono- to tetracyclic, especially mono- or bicyclic radicals, described as red pigments with high color purity, high color strength and good resistance, such as light, weather, heat and migration resistance are.
- the good suitability of such products as pigments with an orange to, in particular, red shade is also confirmed in numerous subsequent patents, such as, for example, in US Pat. No. 4,579,949, US Pat. No. 4,720,305, US Pat. No. 4,810,802, US Pat. No. 4,783,540, US Pat .
- the present invention accordingly relates to diketopyrrolo [3,4-c] pyrroles of the formula wherein R1 and R2 are independently hydrogen, halogen, C1-C6-alkyl, cyano or a group -OR3, -COOR3, -CON (R3) (R4), -COR3 or -N (R3) (R4) and R3 and R4 independently of one another are hydrogen, C1-C6-alkyl, unsubstituted or substituted by halogen or C1-C6-alkyl phenyl.
- any substituents are halogen, they are e.g. for iodine, bromine, fluorine or especially chlorine.
- C1-C6 alkyl is e.g. for methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, tert-butyl, n-pentyl, tert-amyl or n-hexyl.
- 1,4-diketopyrrolo [3,4-c] pyrroles according to the invention are of particular interest of formula I, wherein R1 is hydrogen, chlorine, bromine, methyl, cyano, -N (R3) 2 or -OR3 means R2 is hydrogen and R3 is hydrogen or methyl.
- the pigments of the formula I according to the invention in which R 1 and R 2 are hydrogen are preferred mean.
- Preferred positions of substituents are the 2-, the 3-, the 6- and the 7-position on the phenanthryl system.
- the diketopyrrolo [3,4-c] pyrroles of the formula I according to the invention can be prepared analogously to generally known processes, for example by reacting a succinic diester with a nitrile of the formula in the required ratio, as known, for example, from US Pat. No. 4,579,949.
- nitriles of the formula II are known compounds. Should some of which are still new, they can be used in analogy to generally known methods getting produced.
- the diketopyrrolo [3,4-c] pyrroles according to the invention can be used as pigments for coloring of high molecular weight organic material.
- High molecular weight organic materials with the diketopyrrolo- [3,4-c] pyrroles according to the invention can be pigmented, e.g. Cellulose ethers and esters, such as Ethyl cellulose, nitrocellulose, cellulose acetate, cellulose butyrate, natural resins or Synthetic resins, such as polymerization resins or condensation resins, such as aminoplasts, in particular urea and melamine-formaldehyde resins, alkyl resins, phenoplasts, Polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polytetrafluoroethylene, Polyamides, polyurethanes, polyesters, polyether ketones, polyphenylene oxides, rubber, Casein, silicone and silicone resins, individually or in mixtures.
- Cellulose ethers and esters such as Ethyl cellulose, nitrocellulose, cellulose acetate, cellulose butyrate, natural resins or Synthetic
- the aforementioned high molecular weight organic compounds can be used individually or in Mixtures as plastic masses, melts or in the form of spinning solutions, lacquers, Paint or printing inks are available. It turns out depending on the purpose as advantageous, the inventive diketopyrrolo [3,4-c] pyrrole as a toner or in Use form of preparations. Based on the high molecular weight to be pigmented The diketopyrrolo [3,4-c] pyrroles according to the invention can be used in organic material an amount of 0.01 to 30% by weight, preferably 0.1 to 10% by weight.
- the high-molecular organic ones are used to pigment paints and printing inks Materials and the diketopyrrolo [3,4-c] pyrroles according to the invention, if appropriate together with additives such as fillers, other pigments, Siccatives or Plasticizers, in a common organic solvent or solvent mixture finely dispersed or dissolved. You can do it in such a way that you have the individual Components for themselves or several dispersed or dissolved together, and only then brings all the components together.
- the dyeings obtained for example in plastics, fibers, paints or prints, are characterized by good general properties such as high color strength, good dispersibility, good overpainting, migration, heat, light and weather resistance, as well as with a good sheen.
- a mixture of 1.0 g of the pigment obtained according to Example 1, 1.0 g of antioxidant (IRGANOX® 1010, CIBA-GEIGY AG) and 1000 g polyethylene HD granulate (®VESTOLEN 60-16, HUELS) is placed in a glass bottle on a Premixed roll bench. The mixture is then passed in two passages on a single-screw extruder extruded, the granules obtained in this way are injection molded (Allround Aarburg 200) sprayed into sheets at 220 ° C and pressed for 5 minutes at 180 ° C. The Press plates have strong yellow shades with good resistance.
- 0.6 g of the pigment obtained according to Example 1 is mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of dibutyltin dilaurate and 2 g of titanium dioxide are mixed and processed into a thin film on a roller mill at 160 ° C. for 15 minutes.
- the yellow PVC film produced in this way is strong in color and lightfast.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH330594 | 1994-11-04 | ||
| CH330594 | 1994-11-04 | ||
| CH3305/94 | 1994-11-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0710705A1 true EP0710705A1 (fr) | 1996-05-08 |
| EP0710705B1 EP0710705B1 (fr) | 1999-12-22 |
Family
ID=4253116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP95810665A Expired - Lifetime EP0710705B1 (fr) | 1994-11-04 | 1995-10-27 | Pigments jaunes de diketopyrrolopyrrole |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5672716A (fr) |
| EP (1) | EP0710705B1 (fr) |
| JP (1) | JP3919248B2 (fr) |
| KR (1) | KR960017668A (fr) |
| CA (1) | CA2161997A1 (fr) |
| DE (1) | DE59507473D1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006342167A (ja) * | 2000-01-06 | 2006-12-21 | Toray Ind Inc | ジケトピロロ［３，４−ｃ］ピロール誘導体 |
| US20070031358A1 (en) * | 2003-10-17 | 2007-02-08 | Olof Wallquist | Cosmetic formulations comprising diketo diphenyl pyrrolo-pyrrole pigments |
| CN1867314A (zh) * | 2003-10-17 | 2006-11-22 | 西巴特殊化学制品控股公司 | 包含二酮基吡咯并吡咯颜料的化妆品制剂 |
| US20070031353A1 (en) * | 2003-10-17 | 2007-02-08 | Olof Wallquist | Cosmetic formulations comprising diketo diphenyl pyrrolo-pyrrole pigments |
| US9751107B2 (en) * | 2012-03-21 | 2017-09-05 | Valspar Sourcing, Inc. | Two-coat single cure powder coating |
| JP2023127878A (ja) * | 2022-03-02 | 2023-09-14 | 東洋インキＳｃホールディングス株式会社 | ジケトピロロピロール顔料、顔料組成物、着色組成物、カラーフィルタおよびセンサ |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415685A (en) | 1981-03-20 | 1983-11-15 | Ciba-Geigy Corporation | Process for dyeing high-molecular organic material, and novel polycyclic pigments |
| US4579949A (en) | 1982-05-17 | 1986-04-01 | Ciba-Geigy Corporation | Preparation of pyrrolo[3,4-c]pyrroles |
| US4720305A (en) | 1984-11-07 | 1988-01-19 | Ciba-Geigy Corporation | Mixtures of pigments |
| US4783540A (en) | 1986-08-07 | 1988-11-08 | Ciba-Geigy Corporation | Solid solutions of pyrrolo-(3,4-C)-pyrrols |
| US4810802A (en) | 1986-01-31 | 1989-03-07 | Ciba-Geigy Corporation | Process for the preparation of brominated pyrrolo-[3,4-c]-pyrroles and mixtures thereof |
| DE3908312A1 (de) * | 1989-03-14 | 1990-09-27 | Langhals Heinz | Neue fluoreszierende perylen- und diketopyrrolopyrrol-farbpigmente |
| US5200528A (en) | 1991-04-26 | 1993-04-06 | Ciba-Geigy Corporation | Diketopyrrolopyrroles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2802338B2 (ja) * | 1988-07-29 | 1998-09-24 | リーデル―デ・ヘーン・アクチェンゲゼルシャフト | 新規の１，４−ジケトンピローロピロール染料 |
-
1995
- 1995-10-27 EP EP95810665A patent/EP0710705B1/fr not_active Expired - Lifetime
- 1995-10-27 DE DE59507473T patent/DE59507473D1/de not_active Expired - Lifetime
- 1995-10-31 US US08/551,192 patent/US5672716A/en not_active Expired - Lifetime
- 1995-11-02 CA CA002161997A patent/CA2161997A1/fr not_active Abandoned
- 1995-11-02 JP JP28546995A patent/JP3919248B2/ja not_active Expired - Fee Related
- 1995-11-03 KR KR1019950039577A patent/KR960017668A/ko not_active Application Discontinuation
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415685A (en) | 1981-03-20 | 1983-11-15 | Ciba-Geigy Corporation | Process for dyeing high-molecular organic material, and novel polycyclic pigments |
| US4579949A (en) | 1982-05-17 | 1986-04-01 | Ciba-Geigy Corporation | Preparation of pyrrolo[3,4-c]pyrroles |
| US4720305A (en) | 1984-11-07 | 1988-01-19 | Ciba-Geigy Corporation | Mixtures of pigments |
| US4810802A (en) | 1986-01-31 | 1989-03-07 | Ciba-Geigy Corporation | Process for the preparation of brominated pyrrolo-[3,4-c]-pyrroles and mixtures thereof |
| US4783540A (en) | 1986-08-07 | 1988-11-08 | Ciba-Geigy Corporation | Solid solutions of pyrrolo-(3,4-C)-pyrrols |
| DE3908312A1 (de) * | 1989-03-14 | 1990-09-27 | Langhals Heinz | Neue fluoreszierende perylen- und diketopyrrolopyrrol-farbpigmente |
| US5200528A (en) | 1991-04-26 | 1993-04-06 | Ciba-Geigy Corporation | Diketopyrrolopyrroles |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0710705B1 (fr) | 1999-12-22 |
| DE59507473D1 (de) | 2000-01-27 |
| CA2161997A1 (fr) | 1996-05-05 |
| JP3919248B2 (ja) | 2007-05-23 |
| JPH08245897A (ja) | 1996-09-24 |
| KR960017668A (ko) | 1996-06-17 |
| US5672716A (en) | 1997-09-30 |
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